27 deals from our U.S. site*
* Taxes and fees may be additional.
Source: CheapCaribbean.com

Trade time at the office for four nights at the beach -- including unlimited meals and drinks.

Select dates September-February
 
Source: Vacation Express

Thanks to one of the lowest Cabo prices we've seen in years, a four-night all-inclusive escape is within reach for as little as $499 per person

Select August-December departures
 
Source: Online Vacation Center

Sail in a balcony cabin aboard Oceania Cruises with a deal that offers prepaid gratuities, $200 in onboard credit per cabin and stops in exotic ports.

Dec. 12; +$600-$1100 December-February dates
 
Source: Starwood Hotels and Resorts

Explore the “undisputed cultural capital of Latin America” (Fodor’s) from one of these popular hotels and save up to 50% compared to weekday stays.

Most weekends through December
 
Source: Starwood Hotels and Resorts

Visit “Mexico’s prettiest resort town” (Fodor’s) and save up to 50% on peak-season rates with this sale from Starwood Hotels and Resorts.

Travel options through December
 
Source: Cruises.com

Sail roundtrip Miami, stopping in Key West and Cozumel

Sept. 21; +$40 Sept. 14, 28; Nov. 30
 
Source: Best Price Cruises

Cruise from Houston to Cozumel, Belize City and Roatan with a deal that has it all: an upgraded cabin, credit and open bar.

Depart Jan. 23; from +$10 nearby dates
 
Source: The St. Regis Punta Mita Resort

Retreat to the St. Regis Punta Mita Resort, renowned for impeccable service and an idyllic locale, and save 40% on peak season rates.

Travel most dates through Sept. 28; 4 nt. min.
 
Source: MSC Cruises

From Costa Rica to the Caymans, Mexico to St. Maarten, MSC Cruises cover the Caribbean with its distinct style. Snag deals with diverse itineraries.

Select 2015-2016 dates
 
Source: Alamo Rent A Car

Destinations on sale include Mexico, Costa Rica, Argentina, Brazil, Peru, Dominican Republic and Aruba

Through April 30
 
Source: iCruise.com

Escape all the holiday stress and island hop through the idyllic Caribbean. Possible stops include Mexico, Key West, Nassau and Grand Cayman.

Select November and December 2015 dates
 
Source: Best Price Cruises

Sail aboard the Norwegian Jewel roundtrip Los Angeles to Cabo, Mazatlan and Puerto Vallarta.

Depart Nov. 15
 
Source: Karisma Hotels & Resorts

Enjoy deep discounts and $150 in credit at two posh all-inclusive beach resorts in Mexico's Riviera Maya with Karisma Hotels & Resorts' flash sale.

Travel through March 2016
 
Source: Sheraton Hacienda del Mar Golf & Spa Resort

Save up to 60% on peak season rates through fall at the 4-star Sheraton Hacienda del Mar Golf & Spa Resort, Los Cabos.

Most dates through Oct. 12
 
Source: Featured Destination: Mexico's Beaches

Deals through December
 
Source: Holland America Line

Take an extensive vacation, stopping in far-flung South American ports from Ecuador to Chile.

Oct. 7
 
Through November
Major Airlines on Fly.com
 
 
 
 

Compare Hotel Rates

Travelzoo Tips

Anna Heinemann — Travel, Entertainment and Local Deal Expert
Anna Heinemann
Deal Expert, Chicago
So get your travel dates set and start planning early for the best opportunities. More